Derivatives of 5-(indol-3-yl)hydantoin

Abstract

Derivatives of 5-(indol-3-yl)hydantoin characterized by the generic structural formula, ##STR1## and their pharmacologically compatible salts are useful in the treatment of cardiac arrythmias in individuals for whom such therapy is indicated. In the preceding structural formula, A is a hydrogen atom, a halogeno, alkyl, hydroxyl, or an alkoxyl radical; n is 0 or 1; R is a hydrogen atom or a phenyl group; X is a methylene, ethylene, trimethylene, or 2-hydroxytrimethylene radical; and Z is a monoalkylamino radical containing 1-4 carbon atoms, a dialkylamino radical containing 2-8 carbon atoms, a morpholino, piperid-1-yl, 4-phenyl-piperid-1-yl, or a 4-hydroxy-4-phenyl-piperid-1-yl radical.

What is claimed is: 
     
       1. A compound having the formula, ##STR23## or a nontoxic, pharmacologically compatible salt thereof, in which: A is a hydrogen atom, a halogeno, a hydroxyl, an alkyl, or an alkoxyl radical, the latter two of which contain 1-4 carbon atoms; n is 0 or 1;   R is a hydrogen atom or a phenyl radical;   X is a methylene, ethylene, trimethylene, or 2-hydroxytrimethylene radical; and   Z is a morpholino, piperid-1-yl, 4-phenylpiperid-1-yl or 4-hydroxy-4-phenylpiperid-1-yl.   
     
     
       2. A compound having the formula, ##STR24## or a nontoxic, pharmacologically compatible salt thereof, in which: A' is a hydrogen atom, a halogeno or an alkoxyl radical containing 1-4 carbon atoms; n is 0 or 1;   R is a hydrogen atom or a phenyl radical;   X' is a trimethylene or a 2-hydroxy-trimethylene radical; and   Z is a morpholino, piperid-1-yl, 4-phenylpiperid-1-yl or 4-hydroxy-4-phenylpiperid-1-yl.   
     
     
       3. The compound as in claim 1, 5-[(indol-3-yl)methyl]-3-[(3-morpholino)propyl]hydantoin. 
     
     
       4. The compound as in claim 1, 5-[indol-3-yl)methyl]-3-[(3-morpholino)propyl]hydantoin hydrochloride. 
     
     
       5. The compound as in claim 1, 5-(indol-3-yl)-3-[3-piperid-1-yl)propyl]hydantoin. 
     
     
       6. The compound as in claim 1, 5-(indol-3-yl)-5-phenyl-3-[3-(piperid-1-yl)-propyl]hydantoin. 
     
     
       7. The compound as in claim 1, 5-(indol-3-yl)-5-phenyl-3-[3-(piperid-1-yl)-propyl]hydantoin hydrochloride. 
     
     
       8. The compound as in claim 1, 5-(indol-3-yl)-3-[(4-phenylpiperid-1-yl)propyl]hydantoin. 
     
     
       9. The compound as in claim 1, 5-(indol-3-yl)-3-[(4-phenylpiperid-1-yl)propyl]hydantoin oxalate. 
     
     
       10. The compound as in claim 1, 3-[3-(4-phenylpiperid-1-yl)propyl]-5-[(indol-3-yl)methyl]hydantoin. 
     
     
       11. The compound as in claim 1, 3-[3-(4-phenylpiperid-1-yl)propyl]-5-[(indol-3-yl)methyl]hydantoin methiodide. 
     
     
       12. The compound as in claim 1, 5-[(5-chloroindol-3-yl)methyl]-3-[3-(4-phenylpiperid-1-yl)propyl]hydantoin 
     
     
       13. The compound as in claim 1, 5-[(5-chloroindol-3-yl)methyl]-3-[3-(4-phenylpiperid-1-yl)propyl]hydantoin hydrochloride. 
     
     
       14. The compound as in claim 1, 5-[(5-methoxyindol-3-yl)methyl]-3-[3-(4-phenylpiperid-1-yl)propyl]hydantoin. 
     
     
       15. The compound as in claim 1, 5-[(5-methoxyindol-3-yl)methyl]-3-[3-(4-phenylpiperid-1-yl)propyl]hydantoin oxalate. 
     
     
       16. The compound as in claim 1, 5-(indol-3-yl)-5-phenyl-3-[3-(4-phenylpiperid-1-yl)propyl]hydantoin. 
     
     
       17. The compound as in claim 1, 5-(indol-3-yl)-5-phenyl-3-[3-(4-phenylpiperid-1-yl)propyl]hydantoin maleate. 
     
     
       18. The compound as in claim 1, 3-[3-(4-hydroxy-4-phenylpiperid-1-yl)propyl]-5-[(indol-3-yl)methyl]hydantoin. 
     
     
       19. The compound as in claim 1, 3-[3-(4-hydroxy-4-phenylpiperid-1-yl)propyl]-5-[(indol-3-yl)methyl]hydantoin oxalate. 
     
     
       20. 5-[(Indol-3-yl)methyl]-3-[3-(piperid-1-yl)propyl]hydantoin. 
     
     
       21. 5-[Indol-3-yl)methyl]-3-[3-(piperid-1-yl)propyl]hydantoin oxalate.